How do I tell a friend that she looks unprofessional and that it’s hurting her job search? We are former colleagues, so I know her work well. She is bright, capable, friendly, and well-liked in her current job but she’s been there a long time without a raise and is ready to move on. I would not ordinarily get involved, but she asked me to help her because she gets interviews, but has not been offered a job yet.

She wears makeup I can only describe as garish, as in, she shaves off her eyebrows and draws them back in. Her foundation is the wrong color and is noticeably a different shade from her complexion. Her clothes are often too tight for her figure. She’s very fit but if it’s too small, it’s too small. We are in a conservative city, and her fingernails are just over the top. They are long and pointy and covered in rhinestones and glitter.Is there a tactful way I can mention these things? I’m sure she’d get a job offer if her appearance were more polished.

I used to know this girl who was smart and capable and was a co-worker of my good friend. Her nickname, no joke, was Mensa, because she insisted that she was a Mensa member, but no one really believed her because she looked like a hooker. Her hair was a vibrant shade of yellow never before seen in nature, her sizable bosom struggled to escape from her teeny, tiny, stretchy little v-neck tank tops, her skirts were no bigger than a napkin, and didn’t leave the house in any less makeup than last year’s winner of RuPaul’s Drag Race. Lovely girl, hideous style.

I would love to live in a world where women could wear whatever they want to work and be judged on their performance and not on the fact that you can see the outline of their areola through their t-shirt. But sadly, in the corporate world, you don’t want to knock on someone’s office door and have them wonder if you’re there to give them the latest market research report or a lap dance.

Here is the tactful way you mention it:

“You have such a great personal style, and I love that you express your personality through your clothes. I’m worried, though, that people aren’t taking seriously because you’re not quite conservative enough; people around here are soooooooo uptight.” Then offer to loan her your black suit, go makeup shopping together and get your faces done, go out together for manicures that don’t involve glitter, and then compliment her excessively on her new look. Make sure to tell her she can use you as a reference any time because you know how amazing and smart she is. Even if she gets mad, I guarantee you she’ll think about what you said the next time she gets dressed for a job interview.